Chirality Sensing of Chiral Carboxylic Acids by a Ureido-linked Zinc Bisporphyrinate.

Abstract

We designed and synthesized a ureido-linked zinc bisporphyrinate [Zn2(UBis)]. CD spectra show that this zinc bisporphyrinate has the ability to sense the chirality of chiral carboxylic acids without derivatization. Our studies suggest that the phenyl ring in the linker forms π-π interactions with porphyrin planes and that the carboxylic acid is coordinated to the zinc in the host-guest complex. DFT calculations show that the bisporphyrin adopts a "Z"-shaped configuration, and that the ureido group forms hydrogen bonds with carboxylic acids. The combination ofπ-π interactions, coordination interactions and hydrogen bonding interactions leads to the chirality sensing ability of [Zn2(UBis)].